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27QuestionsThatWillChangeYourLife!

Jan Johnston Osburn
Jan Johnston Osburn Mogul Influencer | Career & Life Coach | Helping People Turn Dreams into Realities
1y Washington, DC, United States Story
27 Questions That Will Change Your Life!

When Was The Last Time You Had A Conversation With Yourself?

Conversation. A form of communication.  It’s like a tennis match.  One person says something and the other person responds.  It goes back and forth like that.  

Sometimes it’s friendly banter - those short clever sentences, snazzy comebacks, or even flirtatious teasing. Sometimes it’s a deeper dialogue focused on one topic and at other times, it’s sharing sentiments on a number of subjects.

But, it’s the conversations we have with ourselves that are the most meaningful and life-altering  -  if you agree to brutal honesty and assessment.   

Questions are powerful tools because they invoke insights and discoveries. They also jump start our pursuit to divulge the most relevant-sometimes unimagined- information we need to focus on our current state of being.

So, turn the tables today.  Have a key conversation with yourself and see where it leads. Ask yourself these 27 questions and then answer them with unabashed reflection. Take the opportunity to challenge your own ideals and to shed light on your gap between where you are and who you want to be.   

27 Questions to Change Your Life

  1. Let’s say that you cannot fail. Given that premise, what things would you now do?
  2. Take a few minutes to think back over your life. At what times have you felt the most alive? And, why? What made those times electric?
  3. What things (subjects, acts, events) are you avoiding in your life right now? Why? What will happen if you stop avoiding them?
  4. What dream do you continue to ignore but it keeps coming back to you anyway? Why do you continue to ignore it?
  5. Do you find yourself influencing your world, or does your world (environment, etc.) influence you?
  6. When do you feel at your best? What things are you then doing? What people are you around at these times?
  7. What is the story you are writing for yourself each day?
  8. Do you believe you are the author of your life? Penning your own story?
  9. What price are you willing to pay for giving up or living your dream?
  10. Can you list your values in life? What are they?
  11. Does your career and life align to those core values?
  12. What things keep you up at night worrying?  What things do you lie in bed thinking about at night?
  13. Are you the kind of friend you’d want to have as a friend?
  14. Are you the kind of person that you would like to meet?
  15. In what ways do you sabotage your success?
  16. In what ways do you allow other do sabotage your success?
  17. What do you actually want out of life?
  18. Do you constantly dwell on and relive the past? What things, people, events, and places do you hold on to out of habit that no longer feels good?
  19. Do you surround yourself with positive, life-affirming people / friends who want the best for you?
  20. How do you feel when you are out with your friends? Do you feel energized and ready to meet your goals or do you feel drained in negative?
  21. Do your friends support your success?
  22. What do you want to be remembered for at the end of your life? Does that match how you are living today?
  23. What can you do right now that would make the biggest impact to living your ideal life?
  24. Why don’t you do the things you know you should be doing?
  25. If you were not going to be successful achieving your dreams, what would you say would be the reasons why it wouldn’t happen?
  26. What lies do you tell yourself? (By the way, excuses are simply lies we tell ourselves to justify our behavior.)
  27. Why were you put on earth?

Whew! You’re done.

Did anything surprise you, worry you, or is anything impacting your well-being? 

If so, what are you going to do about it?

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3 comments

  • VivianaVizcaino
    VivianaVizcaino Viviana
    1y ago

    This is a really great compilation. I think setting time aside to ask myself a few of these daily will make a noticeable difference. Thank you for your input!

    This is a really great compilation. I think setting time aside to ask myself a few of these daily will make a noticeable difference. Thank you for your input!

    • Jan Johnston Osburn
      Jan Johnston Osburn Mogul Influencer | Career & Life Coach | Helping People Turn Dreams into Realities
      1y ago

      Thank you, Viviana, for reading. Some of my favorite coaching questions. They're also really great for self-reflection -- but you have to be brutally honest with yourself!

      Thank you, Viviana, for reading. Some of my favorite coaching questions. They're also really great for self-reflection -- but you have to be brutally honest with yourself!

  • Lost_ Yank911
    Lost_ Yank911 Random thoughts from an EMT
    12mo ago

    Wow, got me thinking! What happens if all my answers are admitting to living a lie? Just merely existing.

    Wow, got me thinking! What happens if all my answers are admitting to living a lie? Just merely existing.


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Jan Johnston Osburn
Mogul Influencer | Career & Life Coach | Helping People Turn Dreams into Realities

Johnston Osburn is a Career and Life Coach who helps people turn dreams into realities. After years as a Global Talent Acquisition Professional, she realized how frequently people limit themselves because they lack belief in their abilities. They are afraid to dream, let alone dream big. [...]

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